title: Solid-phase peptide synthesis and solid-phase fragment coupling mediated by isonitriles.
abstract: The synthesis of polypeptides on solid phase via mediation by isonitriles is described. The acyl donor is a thioacid, which presumably reacts with the isonitrile to generate a thio-formimidate carboxylate mixed anhydride intermediate. Applications of this chemistry to reiterative solid-phase peptide synthesis as well as solid-phase fragment coupling are described.
authors.affiliation: Laboratory of Bioorganic Chemistry, Memorial Sloan-Kettering Cancer Center, New York, NY 10065, USA.
authors.forename: Ting
authors.initials: T
authors.lastname: Wang
authors.forename: Samuel J
authors.initials: SJ
authors.lastname: Danishefsky
mesh_terms: D000577:Amides / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis*; D060327:Solid-Phase Synthesis Techniques / Q000379:methods*; D014667:Vasopressins / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000577:Amides; D009570:Nitriles; D010455:Peptides; D014667:Vasopressins